Water → HCID 67056896, compound

HRID 517510Notes

Reaction equation

HRID 517510 reaction equation
[OH-].[Li+].[CH2:3]([O:7][C:8]1[CH:38]=[CH:37][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:26][CH2:25][N:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:23][CH2:22]2)[C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].O>O1CCCC1>[CH2:3]([O:7][C:8]1[CH:38]=[CH:37][C:11]([C:12]([NH:14][CH2:15][C@H:16]([N:21]2[CH2:22][CH2:23][N:24]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:25][CH2:26]2)[C:17]([OH:19])=[O:18])=[O:13])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86667907HCID 86667907, compound

Product 1

HCID 67056896HCID 67056896, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.6 ml (1.6 mmol) of a 1M aqueous solution of lithium hydroxide are added to a solution of 400 mg (0.8 mmol) of methyl (S)-3-(4-but-2-ynyloxybenzoylamino)-2-[4-(toluene-4-sulphonyl)piperazin-1-yl]propanoate in 5 ml of tetrahydrofuran and the medium is stirred at ambient temperature for 20 h. After addition of water and of acetic acid up to a pH of 4, the reaction medium is extracted with ethyl acetate. The organic phase is dried over sodium sulphate then filtered and concentrated under vacuum. 400 mg (100%) of (S)-3-(4-but-2-ynyloxybenzoylamino)-2-[4-(toluene-4-sulphonyl)piperazin-1-yl]propanoic acid are obtained in the form of a white solid.

Workup

  1. extractionof acetic acid up to a pH of 4, the reaction medium is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationthen filtered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-813f075cda7a4f1aba551386150e229f
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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